149035-74-5Relevant academic research and scientific papers
Synthesis of the Fjord-region cis- and trans-Amino Triol Derivatives of the Carcinogenic Hydrocarbon Benzochrysene and Utilization for the Synthesis of a Deoxyadenosine Adduct Linked to the N6-Amino Group
Kiselyov, Alexander S.,Steinbrecher, Thomas,Harvey, Ronald G.
, p. 6129 - 6134 (1995)
Efficient syntheses of the complete set of four diastereomeric fjord-region amino triol derivatives of benzochrysene in which the amino group in the 14-position and the adjacent 13-hydroxyl group are trans or cis to one another (trans- and cis-5 and 6) is described.This is the first description of the syntheses of the bay- or fjord-region cis-amino triol derivatives of any carcinogenic polycyclic aromatic hydrocarbon (PAH).The amino triols are key synthetic precursors of PAH-oligonucleotide adducts in which the PAH moiety is covalently linked to the exocyclic amino groups of deoxyadenosine or deoxyguanosine.Formation of adducts of this type via reaction of a PAH diol epoxide metabolite with DNA is believed to be a critical step in the mechanism of PAH carcinogenesis.The synthetic amino triol isomers may be used to synthesize PAH-oligonucleotides needed for site-directed mutagenesis studies to relate isomer structural differences to their effects on DNA replication.
Wavelength-selective uncaging of da and dC residues
Schaefer, Florian,Joshi, Khashti Ballabh,Fichte, Manuela A. H.,MacK, Timo,Wachtveitl, Josef,Heckel, Alexander
, p. 1450 - 1453 (2011/05/15)
Nitrodibenzofuran (NDBF) groups are used as photolabile "caging" groups to temporarily mask the Watson-Crick interaction of dA and dC residues. They show improved masking capabilities and are photodeprotected 12 times more efficiently than 1-(o-nitropheny
